The Sweetest Kiss
by Dawnoflight95
Summary: Dean's used to the skirts and the weird excuses. But wearing lipgloss is the last straw. Total PWP. WARNING: Wee!Cest/Underage (Sam's 14), Crossdressing, Genderplay/Feminization & Slash. Rated M for a reason. Wincest.


First time writing Wincest, so don't be too harsh! Taming my addiction to Wee!cest and Fem!Sam in one short fic. Enjoy.

**WARNING!:** Contains underage sex, incest, feminization, genderplay, slash, and an unhealthy obsession with crossdressing.

* * *

_"Try to tell you 'no' but my body keeps telling you 'yes',_  
_Try to tell you 'stop', but your lipstick got me so out of breath._  
_I'll be waking up in the morning, probably hating myself._  
_And I'll be waking up, feeling satisfied, but guilty as hell."_

_~Maroon 5 - One More Night_

* * *

"Sam?"

No response.

"Come on Sammy, I don't have all day!"

"Give me a second, Dean!"

The kid's awkward voice sounds just a bit deeper than it was two weeks ago.

Time flies.

They're growing up too fast. Sam's taking his first "advanced placement" class. His first year in high school and he's already primed to be a nerd. Dean knows it makes no difference to dad, but hey, someone ought to be the brains. Sam delivers.

But not this time. Sam is not delivering. He's stalling. Dean raps on the door again. The door opens after a minute and Sam's pink in the face when he side steps Dean and makes his way to their bedroom; a luxury in this specific motel.

Dean's ignoring Sam face and enters the bathroom. So what if Sam acts like he's been shooting up or sneaking out at night to join a gang?

No wait. Yeah, Dean cares if his little brother's a heroin addict, and he definitely doesn't want the kid to get hurt. But lately? Sam's been getting out of hand and not in the usual complaining sort of way. It's been how he's acting. Just flat out sketchy. Dad just grumbles about it being another "phase" but it makes Dean worry. Only to Dean. The kid's been staying after school, giving bullshit reasons like track meets when it's pouring rain out and the coach's driving home in his pick up truck. Or this new obsession with the bathroom; what gives?

Dean had thought about it long and hard before. Ever since Sam started dressing girlier, he became happier. Dad… wasn't so thrilled. But hey, Sam really got whatever he wanted as long as he didn't tack on a skirt while they went on hunts. So what was causing things to go haywire? Maybe his special time with Sammy was just getting to be too much for him.

Maybe someone found out.

_Fuck it._ Dean shrugs. Sam had his chance to explain. Dean enters the bathroom; a small, dingy room tacked onto the motel. The toilet seat's down (one of Sam's newer habits) so Dean flips it up and unzips his fly. Out and about, Dean stretches his back and rubs his chest down with a yawn and eyes closed. When they open, his gaze shifts to the trash bin to his right. And that's when he sees it.

He's seen it a few times; in cheap drug stores where it's easy to shop lift, in the back seat of every girl's car he's been in or in the front of every jock's dad's car: the outer safety covering of a cosmetic product. Clear, the edges frayed with white lettering.

When Dean finally zips up, he picks the little bit of plastic from the trash. "Watermelon Splash Lip Gloss?"

Something inside Dean's body begins to race. There was no way in hell his father started putting on make up while on hunting trips. Dean himself hasn't brought home a girl in weeks, ever since he and Sammy started their little sessions. Either Sam is seeing a girl or is being a girl. The first makes his blood boil. The second makes his dick twitch.

He looks at the wrapping in his hand, the images coming all too easily. He can just picture Sam's mouth, lined in pink and red, wrapped around his cock. _Ah, fuck._ Dean shakes his head quickly and walks out of the bathroom to the room he shares with his little brother. The door's closed, but he hears Sam shifting things around inside. As quietly as he can, Dean nudges the door open.

And there he is. Sam is shirtless, facing a mirror, his developing torso stark naked in front of Dean. There's a red and black plaid skirt on his hips, just hanging there, swooshing back and forth when he moves even in the slightest manner. Dean's used to the skirt, he's grown to love the easy access. He's, however, completely new to the lip-gloss. The little brother he's been dreaming about, the sibling he's crawled into bed with countless times with, is only a few feet away, puckering his lips as he applies another coat of lip-gloss. Sam's lips are pinkish, popping out as he runs his delicate tongue over them. Dean swallows and moves forward, coming into his view of the mirror.

Sam sees him in the mirror and drops the tube. "D-Dean, I can-"

"Don't." Dean's voice is harsh and barely audible with the lust that's building inside his head.

"I… I just wanted to try it," Sam says, looking downwards.

Dean tries to look anywhere besides those lips, but all he accomplishes is awkward shifty glances. It only causes panic in Sam. "I just wanted to be pretty. Pretty for y-you," Sam stutters out, his cheeks flushed.

Dean can't believe what he's hearing. He's gonna burst if Sam keeps talking all innocent like, but_ oh fuck_, it sounds so good. It's that voice that shoots pleasure down Dean's spine. "For me, baby girl?"

Sam nods; his cheeks tinted pink at the way Dean calls him baby girl. _Christ._ Even after all this time, all the touching, kissing, Sam's still shy and timid. Dean takes Sam's awkward, bony shoulders with larger hands, rubbing them softly. He can't take his eyes off of those lips and Sam knows it, so Sam's gaze stays downward.

With a gentle thumb, Dean traces the outline of Sam's warm, pink lips, all glossy and sparkly with color. When his thumb accidentally touches Sam's mouth, the sticky substance rubs onto him. Pulling his lower lip down, he puts his thumb into Sam's mouth. "Suck," he instructs."

Sam's so eager to please and gently takes Dean's thumb into his mouth. "Yeah that's right," Dean murmurs. "You'll suck on anything. Such a good girl." Sam moans a little at Dean's words, spurring the older brother on. "Tell me how it tastes, baby girl."

"Fruity," Sam says with a small smile.

"I bet it does," Dean responds back, smearing his thumb across Sam's mouth before he finally plants his own mouth on Sam's. He's right. Watermelon flavors burst against his taste buds, but importantly, under that, the kisses taste like Sammy. They taste like the sweetest dessert, and it's mouthwatering, and it's all for Dean.

Sam's mouth opens under Dean's assault, Dean's tongue dancing, embedding the sensory memory of Sam's taste. The realization that dad's not here at the moment makes Dean so beyond excited, that he pushes Sam against the door and away from him. He knows he looks a little crazy and a whole lotta horny, but Dean pushes that all outta his head.

Dean picks up the tube from the ground. "You like lip-gloss, baby girl?" He doesn't wait for Sam to answer. Taking Sam by his jaw, he squeezes the applicator, the pinkish substance oozing out and onto Sam's lips. Words cannot describe how fucking _sexy_ his Sammy looks with his lips just parted a bit, with his little noises, fuck, it's driving Dean nuts.

Sam's gripping the front of Dean's shirt, he gives his older brother the most desperate look that Dean's ever seen. Dean doesn't break his gaze when his baby brother drops to his knees. "Dean," and _fuck yeah_, Dean knows what Sam wants to do. And because Dean's such a giving person, he let's Sam unbuckle his belt jeans.

It's only in the skirt when Sam takes so much control, but it's never like this. Sam's acting like one of those girls Dean's messed with in the Impala, but this is so much better. Dean feels the confinements of his jeans give and his cock is free and in front of his baby brother.

Sam runs that pink tongue against Dean's length and Dean grits his teeth. "Jeeesssuuusss, Sammy." Dean scoots himself back to prop himself against a wall. Sam takes the head of Dean's cock into his mouth and sucks.

The lip-gloss is sticking all over Dean's cock, but he doesn't mind. With the way Sam's lips curve all pretty like around his dick, Dean could care less as long as Sam keeps sucking. "So fucking pretty Sammy. Prettiest girl I know with your mouth all over me."

Sam only nods, refusing to take Dean out of his moth. "Yeah that's right. Keep those pretty pink lips on my cock." Dean's trying so hard not to shove Sam to the floor so he can down right fuck his mouth, but fucking hell, the way Sam's sucks so perfectly on him. "Sammy…"

His baby brother takes his enlarged member out of his little mouth, just bathing the tip of Dean's cock with his tongue. "You can do it Dean." His voice is so small, but so sure at the same time. "You can use my… mouth… how ever you like."

Dean's shaking his head no, but it's not use. His hips are thrusting on their own, as if they're pleading to feel the wet, warmth of Sam's mouth. But when Sam teasingly licks at his cock, Dean loses it.

"Lift that fuckin' skirt up." Sam obeys; the skirt gets pulled up, tucked into the waistband. There's no underwear underneath, and Dean can see the purplish head of Sam's cock, hard and ready to explode. "Touch yourself!" Dean commands.

"Do it Dean, I can take-". So he does. Dean shoves so quickly back into Sam's mouth that he chokes. Sam's other hand digs into Dean's hip as right hand runs over the tip of his own cock.

Sam's throat constricts around Dean's cock, and Dean fucking loves it so much; his throat is tight and hot and perfect. Dean pulls out, Sam exhales, Sam inhales, and Dean plunges back in. Gagging sounds and Dean's deep breathing are the only sounds in the room besides the creak of the crappy floors and Sam's gulping every time Dean pulls out.

Dean removes himself again. He smacks Sam's cheek with his cock; long strands of spit and pre come glistening all over his member and Sam's face. "Yeah, you love it don't you Sammy?" Dean purposefully smears his cock against Sam's lips, feeling the sticky lip-gloss all over him. "Gotta beg for me to fuck your mouth?"

Sam can't answer because Dean fucks his throat some more. Eyes watering, Sam takes it, lust and passion and desire building in his gaze. Dean groans; with the way Sam's mouth is working, he won't last long.

Pulling out, he pulls Sam up from his knees. Sam wobbles, but lands back into the bed when Dean shoves him around. Dean smirks. Sam grins back. Dean crawls on top of Sam, their cocks brushing.

"Dean, I wanna-"

Dean cuts him off. "You don't deserve it, tryin' to keep secrets from me." He knows Sam's aching to be fucked, and Sam whines at how cruel his older brother can be.

But Dean's got other ideas.

With a strong hand, Dean grasps Sam's cock and strokes. Sam's fingers clench the cheap bed sheets as he closes his eyes. Dean works him fast, his hand moving furiously.

Dean guides Sam's hand to his cock, and together, the brothers stroking each other's cock. Sam leans forward and Dean captures those bruised, still semi coated lips in a kiss. As rough as Dean wants to be, he lives for these kisses. The sweetest kiss.

"Dean," Sam gasps into his older brother's mouth.

"Come on baby girl, come for me, lemme hear those pretty pink lips scream my name."

And they do. Sam's orgasming with Dean's name being the only thing he's saying, moaning. Dean follows, coming all over his baby brother's skirt. Spurt after spurt, their come lands all over Sammy, with heavy breathing and sweat sliding down Dean's brow.

Exhausted and spent, Dean rolls to his side, lying next to his brother. Still shaken by pleasure, Sam curls against Dean. Even though the skirt is sticky, Dean could care less. He kisses Sam's lips once more.

"No more secrets, okay? No more sealed lips."

Sam nods.

"And Sammy?"

"Yeah?"

"You're the prettiest girl in my book. Don't ever change."

Sam licks his lips.

* * *

All thoughts and critiques and "oh my god"s are accepted in review form. Thanks for reading.


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